


Bad Ideas and Worse Decisions

by CrashDevil (cjdevlin19)



Series: Charm, Chocolate, and Cheating [3]
Category: Supernatural RPF
Genre: Angst, Cheating, F/M, Infidelity, Reader-Insert, Smut
Language: English
Status: Completed
Published: 2021-03-11
Updated: 2021-03-11
Packaged: 2021-03-17 18:08:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,597
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29970291
Author URL: https://archiveofourown.org/users/cjdevlin19/pseuds/CrashDevil
Summary: Y/n takes a chance to see her ex-boyfriend Jensen at a Supernatural convention in Dallas. Things take a turn for the worse. PART THREE OF MEANT TO BE/NOT MEANT TO BE!~~~~A microphone was passed around to people as Jared and Jensen picked from those raising their hands. You didn't raise yours. The woman in front of you did.Jensen's eyes focused on her, then moved to you...and his eyebrows went up. He recognized you! His smile went wide and he turned to Jared, whispering away from the mic with his coffee in front of his mouth so people couldn't see what he was saying. "Oh shit, really?" Jared said, away from the mic but loud enough to hear from the third row. Jared leaned back in toward his microphone. "Sorry, we got distracted. An old friend of Ackles' is in the audience and he wasn't expecting her here. What was the question?"The woman repeated and Jared answered as Jensen pulled the cardboard sleeve off of his coffee, writing on the cardboard and folding it in half to hide the writing. "Exactly what Jared said," Jensen agreed as he twisted the cap back on the Sharpie. He pointed at you. "Come'ere," he said, walking to stage right where the stairs were.
Relationships: Jensen Ackles/Reader, Jensen Ackles/You
Series: Charm, Chocolate, and Cheating [3]
Series URL: https://archiveofourown.org/series/2212515
Comments: 4
Kudos: 20





	Bad Ideas and Worse Decisions

**Author’s Note** : This is a part three to [Meant To Be](https://crashdevlin.tumblr.com/post/615022153514041344/meant-to-be) and [Not Meant To Be](https://crashdevlin.tumblr.com/post/617287184397074432/not-meant-to-be). (Links to tumblr...I still don’t have a name for this series yet...someone help!)

 **Story Warnings** : Angst, sads, past breakup, marital discord, regrets, drinking, adultery/infidelity (as in cheating), **NO WIFE HATE! (it’s just a story) 18+! HERE BE SEX!! DON’T READ IF YOU’RE A YOUNG’UN!!!** , unprotected sex

~~~~~~~~~~~~~~~~~~~

You weren't sure it was a good idea. Shit, he probably didn't even remember you. It was a couple months together and it was fourteen years ago...and it was mostly a long-distance relationship anyway. Would he even recognize you?

As many years as he'd been doing the conventions, it had taken you that long to get up the nerve to buy a ticket, come hang out with his fans...see him in person again.

It wasn't like you were completely out of place at the convention. You'd been watching the show since the first season. You knew it just as obsessively as the rest of the plaid-clad people surrounding you. You just had the added knowledge of what Ackles tongue tasted like...at least what it tasted like fourteen years ago.

Your friends never understood how you could watch your ex-boyfriend's TV show and your ex-husband gave you untold shit about it until the day he left you, but you couldn't stop. Kripke created a compelling world and Jensen and Jared had breathed life into the brothers so perfectly.

Your ticket was Gold. Row C on an aisle just in case you needed to run. You were certain you were going to flee. It was a bad choice to come to the con...wasn't it? Even if he did recognize you...what, was he gonna wanna catch up, talk about the little bit of time you had together?

Bad choice or not, you just wanted to see him. You had to. There was just something about him that haunted you.

He and Jared came out and greeted the Gold Q & A with smiles and cups of coffee from Starbucks. The lights stayed on. You got lost in those greenest eyes as he took sips of his coffee. A microphone was passed around to people as Jared and Jensen picked from those raising their hands. You didn't raise yours. Not only did you not have a question, but you didn't want to call attention to yourself. The woman in front of you, though, did have a question.

Jensen's eyes focused on her, then moved to you...and his eyebrows went up. He recognized you! His smile went wide and he turned to Jared, whispering away from the mic with his coffee in front of his mouth so people couldn't see what he was saying. "Oh shit, really?" Jared said, away from the mic but loud enough to hear from the third row. Jared leaned back in toward his microphone. "Sorry, we got distracted. An old friend of Ackles' is in the audience and he wasn't expecting her here. What was the question?"

The woman repeated her question and Jared started to answer it as Jensen pulled the cardboard sleeve off of his coffee and popped the cap off of a Sharpie, writing on the cardboard and folding it in half to hide the writing. "Uh-huh, exactly what Jared said," Jensen agreed as he twisted the cap back on the Sharpie and tucked it into his shirt pocket. He pointed at you. "Come'ere," he said, walking to stage right where the stairs were.

You swallowed and stood, walking along the aisle to the stage and over to the stairs. Everyone was staring as Jensen descended the stairs and wrapped you in a hug. "It's been forever," he whispered.

"Feels like it anyway," you responded.

He pulled back and offered you the piece of cardboard. "Don't have a lot of time, but here. Burn after reading," he said, smirking and rushing back up to the stage. You gave it a quick glance before heading back to your seat, knowing that it was something he definitely didn't want the other fans to get their hands on. **In town a few more days, give me a call** followed by his phone number. You folded it up and tucked it in your back pocket, your cheeks heating up as you walked back to your seat.

Jensen’s eyes kept coming back to you and he smiled every time. It made you happy. “Pay attention,” you mouthed at him, chuckling as he rolled his eyes and looked away.

You waited until after the panel before you went out to your car in the parking lot and pulled the cardboard sleeve from your pocket. You put his number in your phone and sent off a text.

**> >Hey. It’s Y/n.**

The response was almost immediate.

**< <Hey. It was a nice surprise to see you. You still live in town?**

You smiled.

**> >Yep. Not much is different on my end.**

**< <Well, maybe we could get drinks after I'm done here. I'd love to catch up.**

**> >Works for me, Jensen.**

**< <You sticking around for the rest of the con?**

**> >Do you want me to?**

**< <Well, I know those gold tickets aren't cheap. Might as well get your money's worth.**

**> >I’m talking to you again. Seems worth the money.**

**< <My number is worth a thousand bucks to you?**

**> >There’s no way I can answer that question without seeming like a creepy ex-girlfriend so I refrain.**

**< < 😁 You’re not creepy, I promise. I gotta get to photos. If you aren’t coming back in I’ll message you when I get out of here.**

You started to respond with ‘Sounds good, Cowboy’, but you stopped yourself before you sent it. You didn’t want to come off too flirty. This was a married man. A man who left you for the woman that slipped that thick platinum band on his hand. You deleted the ‘Cowboy’ and added a 😊 before sending it.

You went home and took a nap, waking to several texts from Jensen.

**< <You looked amazing, by the way.**

**< <You aged like good whiskey.**

**< <And you changed your perfume. I like it.**

You were a bit stunned by his words. He couldn’t be flirting with you, could he?

**> >Thanks. I needed to change my signature scent after my divorce. Too many memories, if that makes sense.**

It took a few minutes but he eventually sent you a text back.

**< <I’m probably going to be here til around 10. Wanna plan to meet at Lee Harvey’s at 10:30?**

**> >Sure!**

Drinks with a famous, married ex-boyfriend. Nothing weird or crazy there.

You got to the bar at 10:15, snagging a corner booth and settling in. It wasn’t a big deal. Just a drink or two with the guy who broke your heart. After fourteen years, it wasn't a big deal.

"Hey!" Jensen’s voice pulled you from your thoughts and you stood from the booth to greet him as he walked across the near-empty bar. Sunday night didn't really bring out the big crowd at Lee Harvey's. He wrapped you in another hug and squeezed you tightly before he moved to sit on the opposite side of the booth. "I can't believe you were at the convention! That's a lot of trouble to go to just to get in contact with me."

You settled across from him and tapped your fingernail against the table. "Would it be weird if I said I just wanted to see you again? That I wasn't even expecting you to notice or recognize me?"

"How could I not recognize you, Y/n?"

"Um...it's been fourteen years, Jensen...and we weren't together that long. I mean, obviously long enough to make an impression on me."

"On us both." Your eyes snapped to his and he smiled. "I've thought about you, too, ya know? Wondered where you ended up, how your life unraveled. All this time, you were still right here."

"Yep. Same shit, different year." You smiled as you looked away from those gorgeous green eyes. "You, though! You got the wife and the kids and the brewery and Radio Company. You're a real freakin' rock star now!"

He blushed a bit and shook his head. "Nah, I just have a lot of good people holding me up to make me look good."

"How are you _still_ bashful? You should've grown out of that by now!" You smiled. "I’ve seen videos of you singing at the cons, and I've heard your album. You sound amazing, Jensen."

"Thanks." He smiled and licked his lips as a waiter walked over to take your drink orders. "Still drinking Mules, huh?" Jensen said as the waiter walked off to retrieve your Moscow Mule and his whiskey and beer.

“I stopped for a while, went to daiquiris, but Mules got popular a few years ago and I remembered how much I liked them.”

“Well, I’m still beer and whiskey. Not much changed there,” he said, leaning forward. “I can’t believe you’re still here. I wish I’d known.” His eyes sparkled as he looked at you and you just wanted to hide.

“I don’t really see how it would have changed much. I’m sure you haven’t thought about me much over the last fourteen years.”

“Oh, you’re so wrong.” A flash of sadness went through his eyes as he reached up to scratch at his scalp. “I said I’ve thought about you and it wasn’t a lie.” He cleared his throat as the server brought your drinks. “So, tell me about your life, huh? You still have the desk job? And...you said you went through a divorce? Was that a good thing or a bad thing for you?”

“Not the best thing, no,” you answered, picking up your drink and stirring the liquor. “I met Simon a couple years after you broke up with me. We got married in February 2012. He was sick of me before 2014...but he didn’t actually leave me until 2017. He was living with his coworker within two months of moving out. So...it was good for him, I guess.”

“That sucks. I’m sorry.”

“It’s okay.” You shrugged. “Some folks just don’t get to have the happy ending.”

“You’ve got a lot of years left to get to your happy ending, Y/n.”

You shrugged. “It’s okay if I don’t. I’m happy with...most of my life.”

“Yeah.” He nodded in understanding. “Yeah, I get that.”

As the two of you drank, you talked about life, where he was going to be working now that the show was ending, the brewery and other aspects of his life and he asked all about your life, and you told him about your friends and family and the chocolate shop you opened after your divorce.

“You wen’ from a deshk job to a shocolate shop? Nice!”

You could tell he was starting to get drunk by the way his words had started to slur around the edges and he was dancing a bit in the booth. It was probably time to call cabs or best friends to pick you up, but...you just didn’t want it to be over. This was the happiest you could remember feeling in years.

“Yeah. It was really nice. Started as this little mall kiosk and now I’ve got an actual storefront downtown. It’s a tiny storefront, but still.”

“Damn, what’s it called? I’ll have to come taste your wares before I drive home on Tuesday.”

Your face heated up at the way his voice dropped on that last sentence. You shook your head to try to clear it a bit. “Charlie’s Chocolates. It’s equal parts Willy Wonka joke and-”

“Felicia Day fangirling?” he accused and you laughed.

“Yeah. Exactly.”

He licked his lips and took another drink of his whiskey. “I’m glad that’s been working out for you. You deserve to have good things.”

The conversation fell into silence as you both stared down at the dregs of your drinks. You weren’t sure where to go with things now.

“I’m sorry.” The words from his perfect lips made you look up, but he was still looking at his whiskey glass. “What I did to you was-” He looked distinctly Dean Winchester as he chewed on his bottom lip roughly and stared at the liquor. “I wish I hadn’t done it. I didn’t give you a fair shot, Y/n. I try my hardest not to regret the decisions I’ve made that put me where I am, but I just...I’ve regretted walking away from you for years.”

“Jensen, you don’t need to regret-” you started, but you cut off when his eyes raised to look at you.

“I do. I regret it. I never should have...fuck, Danneel wasn’t worth it.”

Your heart was pounding, his words bouncing around in your head. “You’re drunk. Let’s, uh, call you a cab and-”

“I’m not drunk,” he said, shaking his head. You gestured at the whiskey glass and he rolled his eyes. “All right, I’m a little drunk, but I’m not _that_ drunk. I’m...just drunk enough to be honest. There’s a reason Jared knew your name before I said it this morning, Y/n. There’s a reason I was so happy to see you. I’ve missed you so much.”

You gasped and shook your head in disbelief. “We barely spent any time together.”

“I know, but the time we did spend? You were so down-to-Earth and genuine and you didn’t care about what I could do for you or give you...you just wanted to know me and be with me and I threw that away. I’m sorry.”

You stood and sighed. “You know ‘down-to-Earth’ is what you called _her_ , right? When you broke up with me, you called her ‘down-to-Earth’. I don’t know what’s happened in your relationship to make you nostalgic for one that took place almost completely on a computer screen, but...you put a ring on her finger. She gave you three great kids. Whatever’s wrong...you can work through it.”

He smiled tightly as he swirled the last bit of his whiskey in his glass. “Yeah. We’ve been ‘workin’ through it’ for a few years now. Things were okay for a while after the twins were born, but then they went bad again...and I think about you. When Dee and I are fighting, I think of you and how you really _were_ what I thought she was.”

Fourteen years too late. “Jensen.” You wanted to say something, but you had no idea what to say.

He downed the rest of his whiskey and pulled his phone out. “I’ll call a ride. You need one, too?”

“I’ll call Kaylee.”

“I’m glad you’ve still got her.”

“She’s not getting rid of me anytime soon,” you said, with a small smile.

“So, you’re the Misha of the friendship?” he teased and you nodded. His expression went serious again as he looked down at his phone screen. “You mind if I keep your number? Text you every once in a while?”

You knew you should say ‘no’. With everything he said, all the truths he let out, it was probably a bad idea to keep talking, keep in contact, but...how could you say ‘no’ to those pretty green eyes?

“Yeah. You’ve got my number.”

“And can I call sometimes, maybe? So you can hear my voice?” You couldn’t say anything so you just nodded. “Good. And...a hug?”

Again, your brain said ‘bad idea’, but your body spread your arms and wrapped them around his chest. He smelled amazing, better than he had when he hugged you at the convention. He was warm through the layers of his clothes. You wanted to never let him go.

But you did. You pulled away and bid a hasty goodbye before rushing out of the double doors of the restaurant.

~~~~~~~~~~~~~~~~~~~~~~~

"Slippery slope, sweetie," Kaylee said at lunch the next day. "He's married!"

"We're just texting, that's all. I'm not going to do anything bad. _He's_ not gonna do anything bad. He was just drunk last night, that's all. I'm sure he doesn't really want-"

"Right. Sure. Your famous ex-boyfriend gave you a speech about how you were the only one he's been with that didn't use him for what he could give you and that was just the whiskey. Girl, shut up." She rolled her eyes aggressively and picked up a fry. "You wanna act like he's not stuck on you, fine, but don't act like there's no chance that _you_ might slip up."

"Slip up on what? What do you think I'm gonna do with my famous ex-boyfriend? I'm gonna talk with him, likely from a distance of several thousand miles. That's all we _ever_ did."

“Uh-huh, and you never wanted to change that, right? You never cried about how you never even got to go to second base with him and never would because he broke up with you? You’re never-”

“I’m not a homewrecker, Kaylee. Come on.”

“I’m not saying you are, just...I know he’s the one that got away, ya know?”

You took a bite of your salad and sighed. You were just happy to be able to have any kind of relationship with him, be that friendship or...something more inappropriate. You’d never admit it to your best friend, though. If Jensen had said those things sober, you might have been eager to believe him. You might have been eager to give him what he wanted. But he wasn’t sober.

“He’s definitely the one that got away, but we’re different people now. We’re not slipping down any slopes. We’re just talking.”

She sighed and shook her head. “Just keep your distance. I remember how fast you fell for him before. He’s...got some damn magic over you. Be careful.”

You nodded. ‘Some damn magic’ was a good phrase for it. “I’ll be careful,” you promised, standing and picking up the trash from your lunch. “I gotta get back. Sarah-Beth needs to get off at 1 today or she won’t make it to her 2 pm class. I’ll call you later.”

“Love you, hon.”

You tossed your trash before walking across the courtyard to your small storefront with the Wonka font saying **Charlie’s Chocolates**. You sent your employee, Sarah-Beth, home with a smile and took over the counter, busying yourself with dipping gummy bears in milk chocolate. It was a slow day, Tuesdays generally are, so you put music on and started humming as you roughly chopped peanuts to go across the top of your peanut-butter mountain bars.

You looked up as the bell over the door dinged, automatically ready to welcome a customer, but your cheeks went hot and the greeting stuck in your throat as your eyes fell on Jensen’s smiling face.

“Nice place you got here,” he said and you licked your lips, pulling off your gloves as you nodded.

“Yeah. My home away from home.” You tossed the gloves in the trash and moved to the counter as Jensen started looking into the cases.

“There a ‘Friends and Family Discount’?” he asked, smirking.

“Yes, but you don’t get that. You get the ‘Broke My Heart Upcharge’.”

He looked up and caught your eyes, smiling as he stood to his full height and licked his bottom lip in between his teeth. “And if I buy out your whole store? Would that make up for it a bit?” You opened your mouth to respond but no response came. “Would you be able to close up and have a sober talk with an old friend?”

“We were never friends, Jensen...and paying me off to-”

“Whoa! This is not a payoff. That was me tryin’ to be cute and obviously missin’ the mark.”

“Obviously.” You scratched at the back of your neck before shrugging. “Sorry. Just a little on edge, I guess.”

“I dropped a bomb last night. I’m sorry.” He smiled softly. “Part of the reason I’m here. Clear the air. So...can you close down for a little bit so we can talk?”

“We talked last night. We talked and I-”

“You think the whiskey was talking and it wasn’t, Y/n,” he interrupted. “So...I’m sober and I wanna talk. Can we flip the sign on the door for a few minutes? Just give me five minutes and then I’ll get out of your hair.”

It was a bad idea...but you nodded. “We can talk in my office.”

He smiled that bright, white, perfection and moved to flip the sign and the lock on the door as you maneuvered around the counter to the single hallway with the stockroom, bathroom, small kitchen, and your tiny office which was once a supply closet. There was just enough room for a small, antique, maple computer desk, a desk chair and a file cabinet. You sat on the top of the file cabinet and pushed the desk chair to him for him to sit in. He looked completely out of place in your small desk chair, but you liked the way his legs bowed as he kicked his feet out in front of him.

“This is not an office. This is a closet.”

“I needed less space for paperwork than I needed for cacao and nuts,” you defended. “Your five minutes is running down.”

“You think about me, right?” He focused on his hands clasped in his lap as you leaned back against the grey wall behind you.

“Why does that matter?”

“Because it does. Because you were married and you thought about me, so why would it be such a big thing that I’m married and I think about _you_?”

“Of course I thought about you. You’re _you_. But I’m...I’m me. You shouldn’t be thinking about me.”

He shook his head. “You’re amazing and I hate that you don’t know that.”

“I do know that, but _you_ don’t, Jensen. You barely know me. You barely knew me fifteen years ago and you definitely don’t know me now.”

“You’re right but I feel like I know you anyway.” He ran his hand across his mouth and popped his lips out in an almost pout before shaking his head. “I love my life, Y/n. I love my kids, I love my fans, I love my friends and...Dee is my friend. I love her like I love Jared and Misha, but we haven’t been in love, love like we had when I married her, for a long time. She’s my partner. She’s my best friend and the mother of my children, but we are not in love anymore. Much as I wish we were...we just can’t fake it anymore. Seein’ you at the con, talkin’ to you at the bar...I always knew you were the one that got away. Now here you are in front of me and I don’t wanna walk away again.”

“The one that got--Jensen, you broke up with me. I didn’t get away. You sent me away...because of Danneel.”

“And I regret that. I have regretted that for years.”

“That doesn’t...that doesn’t change it.” You stood and swallowed thickly. “You made your choice. You chose the woman with everything in common with you.”

“It was a bad choice.” He stood too and you were suddenly right in front of each other, looking into each other’s eyes, tension heavy in the air of the small space. “It was a really bad choice,” he whispered.

It was like time slowed to a crawl as he leaned his head down and pressed his lips to yours. You reached up to push him away, your brain setting off warning signals and telling you to put on brakes but one of his hands dropped to your waist and the other went to curl around the back of your neck and somehow you hit the gas instead. You wrapped your hands in his shirt and pulled him down harder, moaning as his fingertips dug into your skin and your body filled with heat.

Time sped up to compensate for the delay and it seemed like no time at all before your pants were at your ankles and you were bent over, clinging to your desk as he worked two thick fingers in and out of you, nibbling on your earlobe as he told you all about how he’d dreamed of you over the years.

“You’re so fuckin’ wet, Y/n. So fucking tight and perfect. Fuck, baby, I don’t know if you can even take me.”

“J-Jensen, please,” you whimpered.

“You want it?” His breath warmed your cheek further and you shivered. “You want me, Y/n?”

“Please. Please, Jensen. Please.”

“Gotta get you opened up a bit more. Think you can cum on my fingers?” You nodded pathetically and gripped the edge of your desk harder, pushing back against him as he reached his other hand around your body and started rubbing two fingers across your clit.

Your whole body tensed up as your orgasm crashed over you and your breath caught as you heard Jensen’s zipper. You had a zing of anxiety, but it was immediately overtaken by lust as the head of his cock pressed against your entrance. You wanted to tell him to wait. You wanted to tell him to stop, but you couldn’t make yourself say the word, especially once he started stretching your pussy past the limit.

“God, you feel just like I thought you would. So fucking perfect,” he praised.

You moaned his name as he rocked his hips against your ass, grinding into you and making your body jerk under him. He pulled back until he was barely inside of you before slowly pushing back into you, letting out a soft expletive before placing his palms flat on your desk, caging you in with his thick biceps.

“Ready?”

He didn’t wait for your answer before he started thrusting, making you squeal and dig your fingernails into the wood of the desk. He was moving faster than you thought he could, hitting your cervix painfully with each pass as your pussy clutched at him to keep him in place. You went to your tiptoes, instinctively trying to change the angle and lessen the impact on your cervix, but he just leaned over you to put more of his weight on you and press you into the desk more.

It made your eyes roll back, the way he manipulated your body with no effort, the way he made you whimper and whine. He was everything you imagined he was, his thick length spearing into you over and over as you came apart on him like you'd done on your toys imagining him for years.

"You're gonna make me cum with this tight fuckin' pussy." He grunted in your ear and thrust in deep. "Where?"

"Not inside. I'm not on anything," you managed the intelligent answer despite the fact that he'd effectively fucked your brains out.

He let out a 'yeah' before pulling out and stepping back. You turned your head, trying to stand straight on shaking legs as he bent enough to grab a handkerchief from his back pocket and jacked his cock, spilling onto the red cloth square as you fixed your clothes.

There was silence in the small space as he let out harsh little breaths, hips jerking as he came. You swallowed heavily as he tucked himself back into his boxers and jeans. Your eyes met his as he pulled his zipper up.

"Oh God, Jensen. What did we do?"


End file.
